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11-Oxo-mogroside V

Names

[ CAS No. ]:
126105-11-1

[ Name ]:
11-Oxo-mogroside V

[Synonym ]:
(1S,4S,9α,24R)-1-{[6-O-(β-D-Glucopyranosyl)-β-D-glucopyranosyl]oxy}-25-hydroxy-9,10,14-trimethyl-11-oxo-4,9-cyclo-9,10-secocholest-5-en-24-yl β-D-glucopyranosyl-(1->2)-[β-D-glucopyrano&#xD; syl-(1->6)]-β-D-glucopyranoside
11-Oxomogroside V
Estr-5-en-11-one, 17-[(1R,4R)-4-[[O-β-D-glucopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->6)]-β-D-glucopyranosyl]oxy]-5-hydroxy-1,5-dimethylhexyl]-3-[(6-O-β-D-glucopyranosyl-β-D-glucopyra nosyl)oxy]-4,4,9,14-tetramethyl-, (3β,17β)-
Mogroside V, 11-oxo-
11-oxo-mogroside-V
11-Oxomogroside V

Biological Activity

[Description]:

11-oxo-mogroside V is a natural sweetener, isolated from the fruits of Momordica grosvenori, exhibits strong antioxidant activity. It exhibits significant inhibitory effects on reactive oxygen species (O2-, H2O2 and *OH) with EC50 of 4.79, 16.52, and 146.17 μg/mL, respectively.

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Metabolic Disease
Natural Products >> Terpenoids and Glycosides

[Target]

EC50: 4.79 μg/mL (O2-), 16.52 μg/mL (H2O2), 146.17 μg/mL (*OH)[1]


[In Vitro]

11-oxo-mogroside V shows a higher scavenging effect on O2- (concentration at which 50% of chemiluminescence intensity is inhibited [EC50]=4.79 μg/mL) and H2O2 (EC50=16.52 μg/mL) than those of mogroside V. 11-oxo-mogroside V exhibits a remarkable inhibitory effect on *OH-induced DNA damage with EC50=3.09 μg/mL[1].11-oxo-mogroside V, a natural sweetener, isolated from the fruits of Momordica grosvenori, exhibits strong inhibitory effect on the primary screening test indicated by the induction of Epstein-Barr virus early antigen (EBV-EA) by a tumor promoter, 12-O-tetradecanoylphorbol-13-acetate (TPA). 11-oxo-mogroside V exhibits strong inhibitory effect on EBV-EA induction (91.2, 50.9 and 21.3% inhibition at 1000, 500 and 100 mol ratio/TPA concentration, respectively)[2].

[In Vivo]

In the group treated with DMBA, TPA and 11-oxo-mogroside V, only 26.6 and 53.3% of mice bore papillomas even at 10 and 15 weeks of promotion, respectively, and only 1.0 3.3 and 4.7 papillomas are formed per mouse at 10, 15 and 20 weeks of promotion[2].

[Animal admin]

Mice[2] Specific pathogen-free female ICR (6 weeks old) and female SENCAR (6 weeks old) mice are use. The animals (female SENCAR, 6 weeks old) are divided into three groups, 15 mice each. The back of each mouse is shaved with surgical clipper, and the mice are topically treated with peroxynitrite (33.1 μg, 390 nmol, 1 mM NaOH) in acetone (0.1 mL) as an initiation treatment. For groups I (control group) II and III, 1 week after initiation with peroxynitrite, mice are promoted by the application with TPA (1 mg, 1.7 nmol) in acetone (0.1 mL) twice a week. For groups II and III, mogroside V and 11-oxo-mogroside V (0.0025%, 2.5 mg/100 mL) in drinking water is given orally, from 1 week before to 1 week after the initiation treatment with peroxynitrite, respectively. The incidence of papillomas is observed weekly for 20 weeks; the percentages of mice bearing papillomas and the average number of papillomas per mouse are recorded. The type of tumors in our experiment is also checked by the pathologist with the histological examination, and the malignant tumors are not observed at 20 weeks of promotion in our experimental system. The tumor incidence is statistically analyzed by Student's t-test in treated mice and controls.

[References]

[1]. Chen WJ, et al. The antioxidant activities of natural sweeteners, mogrosides, from fruits of Siraitia grosvenori. Int J Food Sci Nutr. 2007 Nov;58(7):548-56.

[2]. Takasaki M, et al. Anticarcinogenic activity of natural sweeteners, cucurbitane glycosides, from Momordica grosvenori. Cancer Lett. 2003 Jul 30;198(1):37-42.


[Related Small Molecules]

Captisol | Cyclosporin A | H2DCFDA | 0MPTP hydrochloride | GW4869 | Etomoxir | TD139 | Mitoquinone mesylate | GSK2795039 | JC-1 | BAPTA-AM | AP 20187 | Setanaxib (GKT137831) | D-Luciferin | Crotaline

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Molecular Formula ]:
C60H100O29

[ Molecular Weight ]:
1285.419

[ Exact Mass ]:
1284.635010

[ PSA ]:
473.51000

[ LogP ]:
-1.52

[ Index of Refraction ]:
1.641

[ Storage condition ]:
2-8℃


Related Compounds